Phillip Smith, TPCP CRPC AIF

05/29/2026

The people who retire confidently aren't always the ones with the most money. They're the ones who did the work across all five areas of a solid retirement plan. This post breaks down exactly what that means.

If you're asking whether you can retire before 65 and make it last, here's how we answer that question across five areas: cash flow, taxes, risk, portfolio, and estate planning.

05/25/2026

Your will is not the last word.

Most people don't know that. Ignorance here is not benign.

There's an order to things in the financial world...a sort of hierarchy you did not create and cannot override with good intentions:

Beneficiary designations on retirement accounts, life insurance policies, and bank accounts sit at the top of that hierarchy. They outrank your will. They outrank your attorney. They outrank whatever you told your spouse you wanted to happen.

The name on the form is the name that gets the money.
This is not a technicality. It is a law of the territory. And the territory does not care about your more recent intentions if the form does not reflect the change in your wishes.

I've seen it:
the ex-spouse who inherits
the deceased parent (and the deceased spouse with no contingency listed)
the sibling whose life looks nothing like it did fifteen years ago (or worse, looks exactly like it did when they were making all those questionable decisions 20 years ago)

Any of them could be first in line. It might not match what you want today, but if you never updated the form...

Maybe nobody told you the beneficiary form outranked the trust or will. Maybe you assumed the system (or someone specific) would honor what you meant rather than what you signed.

That assumption is an abdication of responsibility.

You built something, right? You worked for it. And you have an obligation - to yourself, to the people you love, to any semblance of the legacy you want to leave - to make sure it goes where you intend.

When did you last look at your beneficiary designations?

If the answer is "I'm not sure," that's not a small problem. That is the problem.

Order your house, my friends.

05/20/2026

Has anyone warned you about the first Monday after retirement? Let me be the first...

I hear it's amazing! The first few weeks feel like vacation: unhurried mornings, no alarm, no meetings; the freedom you spent decades working toward.

But those months become something like groundhog weeks. Something shifts, and you feel it...something missing.

The best organizations in the world don't just give people a paycheck. They give them a reason to be there, day in and day out: a sense of belonging. A feeling that what they do matters. Purpose.

When that's gone, even when you chose that special day when you were definitely going to be done, something has to replace it. Life without purpose feels, well, hollow.

Your retirement accounts can be an indicator of being financially prepared. The common retirement plans can help you be strategically prepared. But are you purposefully prepared.

Like, okay, you have the financial side covered, but what about the human side?

The calendar starts to feel different, open yes, but in a way that doesn't quite feel like freedom. The structure that organized your days, your identity, your sense of contribution - it's gone. And if you didn't think about how you were going to spend your time for the next couple of decades, nothing's there to replace it.

Who are you when the title, the schedule, the commitments, and the paycheck all disappear? What does a meaningful day consist of when there isn't work? What gets you out of bed when nothing requires you to?

These are the questions that determine whether retirement actually delivers what you spent decades building toward.

People don't stop needing purpose when they stop working. They just need a new source.

Knowing your why determines what you do when you arrive.

05/18/2026

The financial industry spent decades teaching you how to save.
Has anyone taught you how to stop?

The savings drumbeat is intentional, and it's great while you're working, but it has a design flaw.

Every account, every contribution, every statement you ever received was oriented around a single directive:

Accumulate
Build the pile
Feed the pig
Grow the balance
Hit the number

The entire architecture of modern retirement was constructed around many variations of one instruction: keep saving and don't touch it. So you do that (did that), for decades.

And then one day you retire and the new instruction is, "Now start taking money out."

It's a shock to the system - psychologically and financially.

Why people succeed (or feel successful) in the first half of their career and struggle in the second isn't an issue of competence. It's about preparation. The retirement system prepared you for accumulation. and then didn't offer to prepare you for what comes next.

What comes next is harder, in many ways.

Which account do you draw from first?
How do taxes work when the paycheck stops?
Are you paying more than you should in ?
How does Social Security interact with investment income and your Medicare costs?

Most people don't give these topics the time they deserve. Many will guess. They'll draw from whatever feels most accessible and hope.

The system failed to teach you decumulation. Not 'the system's' fault: it makes more money when your accounts are larger.

But, that does not mean you get to remain ignorant of it. You built something. Hopefully, you feel the obligation to steward it well.

Getting accumulation right matters. Getting retirement income right is what determines whether what you've saved will last.

Retirement may be where the most consequential decisions live. Are you prepared for it?

05/17/2026

Asking for help can feel like retreat.

It can feel like admitting something went wrong.

This can be especially true for people who spent decades being competent, capable, and self sufficient, building careers, families, and financial lives on their own effort and good judgment.

"If anyone thinks he is wise in this age, let him become a fool that he may become wise." ~ 1 Corinthians 3:18

The skills that got you here aren't always the same ones that carry you through what's coming next. Retirement planning, tax strategy, estate clarity, income coordination - these are their own disciplines.

Surrounding yourself with people who know the things that you don't isn't a concession, it's exactly what wisdom looks like in practice.

05/16/2026

Most people decide when to claim Social Security in about 15 minutes.

For a lot of couples, that decision is worth over a million dollars.

Claiming at 62 vs. 70 can more than double your monthly benefit. And if you're the higher earner, that number doesn't just follow you. It follows your spouse for the rest of their life too.

Watch the full breakdown here: https://youtu.be/YdzmCLtQlVw

05/15/2026

We're not always great at seeing the future problems today's actions will create.
But, usually, we're pretty good at solving the problem in front of us.

Every pre-tax dollar going into a 401k or Traditional IRA feels like a win. Lower taxable income today. More money invested now.

The math looks clean. And it's efficient...for now.

But (and it's a big one): every dollar that went in untaxed has to come out taxed (except for that ONE exception, IYKYK and if you don't you can aske me). It's tax deferral, not tax savings.

When Social Security (and PERS, for many Oregonians), required distributions, and investment income all hit in a single year, the tax picture looks nothing like it did during the working years.

The tax break you're getting today might be the tax problem you're ignoring tomorrow.

Great leaders don't just solve today's problem, they anticipate tomorrow's.
Your retirement plan deserves the same thinking. You've got to be the leader in your own life.

The window between retirement and required minimum distributions is one of the most valuable (and most overlooked) opportunities in all of :

-->Whether you convert pre-tax dollars
-->How you manage/source income in those early years
-->i.e. which accounts you draw from, and when

These decisions shape what you keep in your accounts and out of the hands of Uncle Sam, Sister State, and your Aunties IRiS & IRMAA and for the next two decades.

The strategy isn't overly complicated (usually), but it requires someone willing to look a little further down the road than most of us usually do.

05/15/2026

Social Security: The $1 Million Retirement Decision Most People Make in 15 Minutes By Phillip Smith, TPCP® CRPC® AIF® | Financial Planner | Tidepool Wealth Strategies You are 61, maybe 62. You've been working toward this for a long...

05/13/2026

If you're married, when you claim Social Security affects more than your check. Your spouse may be entitled to up to 50% of your full retirement age benefit, and if you claim early and lock in a reduction, you're reducing their check too.

Permanently.

Watch the full episode for the complete breakdown of Social Security claiming strategy, spousal benefits, survivor benefits, and the break even analysis:
https://youtu.be/YdzmCLtQlVw

05/13/2026

Do you think about retirement?
In your 60s, most people who want to retire have a retirement date in mind.

Very few have a retirement plan.

There's a gap in there, and that's where real work begins.

A date feels like progress. It's specific, it's visible, you can count down to it (our family loves setting a calendar countdown for trips and vacation time).

That date, though, is just a destination on a map. It doesn't tell you how to get there. It doesn't tell you what to pack. It doesn't tell you what you'll do when the road looks different (or the turbulence hits harder) than you were expecting.

The people who retire well aren't the ones who successfully ejected on the intended date. They're the ones who spent time thinking about WHAT COMES NEXT.

Day one - what does income look like? Which accounts do you draw from first? What's the deal with healthcare before Medicare? What's the tax picture going to look like in year ten of retirement? How will you spend your time? Who will you spend it with? What things will you finally do (the things put off because there just wasn't enough time while you were working)?

Retirement isn't any more complicated than you want it to be, but giving the questions above a little thought before you exit is important. You spent a lifetime earning this. You've worked to earn a plan that's intentional.

A retirement date is where the journey starts. The plan helps you visualize the journey worth taking.